Ammonium Chloride → HCID 68158215, compound

HRID 243144Notes

Reaction equation

HRID 243144 reaction equation
CC(C)([O-])C.[K+].[CH3:7][N:8]1[CH:12]=[CH:11][C:10]([NH2:13])=[N:9]1.F[C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[N+:22]([O-:24])=[O:23].[NH4+].[Cl-]>C1COCC1>[F:21][C:19]1[CH:18]=[CH:17][C:16]([N+:22]([O-:24])=[O:23])=[C:15]([NH:13][C:10]2[CH:11]=[CH:12][N:8]([CH3:7])[N:9]=2)[CH:20]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 679672,4-DifluoronitrobenzeneHCID 1372541-Methyl-3-aminopyrazoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 68158215HCID 68158215, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Potassium tert-butoxide (898 mg, 8.0 mmol) was added to a stirred solution of 1-methyl-1H-pyrazol-3-ylamine (0.35 mL 4.00 mmol) in anhydrous THF (5 mL) under a nitrogen atmosphere at 0° C. After 15 min 2,4-difluoro-1-nitrobenzene (0.44 mL, 4.0 mmol) in anhydrous THF (5 mL) was added and stirring at 0° C. continued for 1 h. The reaction mixture was poured into a solution of NH4Cl (50 mL). The aqueous phase was extracted with EtOAc (×2) and the combined organic fractions washed with brine, dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-100% EtOAc in cyclohexane) to afford the title compound as a dark red solid (386 mg, 41%). LCMS (Method C): RT 3.29 min [M+H]+ 237.08

Workup

  1. extractionThe aqueous phase was extracted with EtOAc (×2)
  2. washthe combined organic fractions washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-100% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-e5c49b5fc22447e09c82ea420a373f9b
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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